C(sp)-C(sp 3) bond formation through cu-catalyzed cross-coupling of N -tosylhydrazones and trialkylsilylethynes

Journal of the American Chemical Society

Volumn 134, Issue 13, 2012, Pages 5742-5745

  Ye, Fei ^a   Ma, Xiaoshen ^a   Xiao, Qing ^a   Li, Huan ^a   Zhang, Yan ^a   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BOND FORMATION; CARBENES; CROSS-COUPLINGS; MIGRATORY INSERTION;

CHEMISTRY; SYNTHESIS (CHEMICAL);

CATALYSIS;

ACETYLENE; CARBENE; COPPER; HYDRAZONE DERIVATIVE; N TOSYLHYDRAZONE DERIVATIVE; TRIALKYLSILYLETHYNE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION;

EID: 84859331570     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3004792     Document Type: Article

References (35)

1. Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; pp 493-529.
2. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2018
3. Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568
4. Marsden, J. A.; Haley, M. M. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
5. Plenio, H. Angew. Chem., Int. Ed. 2008, 47, 6954-6956
6. The Chemistry of Triple-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1994.
7. Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH, Weinheim, Germany, 1995.
8. Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643
9. Altenhoff, G.; Wurtz, S.; Glorius, F. Tetrahedron Lett. 2006, 47, 2925-2928
10. Vechorkin, O.; Barmaz, D.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 12078-12079
11. Yang, L.; Huang, L.; Luh, T. Org. Lett. 2004, 6, 1461-1463
12. Ohmiya, H.; Yorimitsu, H.; Oshima, K. Org. Lett. 2006, 8, 3093-3096
13. Zhao, Y.; Wang, H.; Hou, X.; Lei, A.; Zhang, H.; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048-15049
14. Cahiez, G.; Gager, O.; Buendia, J. Angew. Chem., Int. Ed. 2010, 49, 1278-1281
15. Chen, M.; Zheng, X.; Li, W.; He, J.; Lei, A. J. Am. Chem. Soc. 2010, 132, 4101-4103
16. Vechorkin, O.; Godinat, A.; Scopelliti, R.; Hu, X. Angew. Chem., Int. Ed. 2011, 50, 11981-11985
17. Hatakeyama, T.; Okada, Y.; Yoshimoto, Y.; Nakamura, M. Angew. Chem., Int. Ed. 2011, 49, 10793-10796
18. Rayabarapu, D.; Tunge, J. J. Am. Chem. Soc. 2005, 127, 13510-13511
19. Bi, H.; Zhao, L.; Liang, Y.; Li, C. Angew. Chem., Int. Ed. 2009, 48, 792-795
20. Zhang, W.; Zhang, X.; Li, J. J. Org. Chem. 2010, 75, 5259-5264
21. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486-7500
22. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560-572
23. Barluenga, J.; Moriel, P.; Valdés, C.; Aznar, F. Angew. Chem., Int. Ed. 2007, 46, 5587-5590
24. Barluenga, J.; Escribano, M.; Aznar, F.; Valdes, C. Angew. Chem., Int. Ed. 2010, 49, 6856-6859
25. Xiao, Q.; Ma, J.; Yang, Y.; Zhang, Y.; Wang, J. Org. Lett. 2009, 11, 4732-4735
26. Brachet, E.; Hamze, A.; Peyrat, J.-F.; Brion, J.-D.; Alami, M. Org. Lett. 2010, 12, 4042-4045
27. Zhou, L.; Ye, F.; Ma, J.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 3510-3514
28. Chen, Z.-S.; Duan, X.-H.; Wu, L.-Y.; Ali, S.; Ji, K.-G.; Zhou, P.-X.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2011, 17, 6918-6921
29. Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 775-779
30. Zhao, X.; Wu, G.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 3296-3299
31. Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 1114-1117
32. Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y.; Ye, F.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 968-971
33. Ye, F.; Shi, Y.; Zhou, L.; Xiao, Q.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 5020-5023
34. Suárez, A.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 3580-3582
35. Yamamoto, Y. Chem. Rev. 2008, 108, 3199-3222